“Called to Second Guess Ourselves”
September 25, 2025
Luke 16:1–13
Then Jesus said to the disciples, ‘There was a rich man who had a manager, and charges were brought to him that this man was squandering his property. So, he summoned him and said to him, “What is this that I hear about you? Give me an account of your management because you cannot be my manager any longer.”
Then the manager said to himself, “What will I do now that my master is taking the position away from me? I am not strong enough to dig, and I am ashamed to beg. I have decided what to do so that, when I am dismissed as manager, people may welcome me into their homes.” So, summoning his master’s debtors one by one, he asked the first, “How much do you owe my master?” He answered, “A hundred jugs of olive oil.” He said to him, “Take your bill, sit down quickly, and make it fifty.” Then he asked another, “And how much do you owe?” He replied, “A hundred containers of wheat.” He said to him, “Take your bill and make it eighty.” And his master commended the dishonest manager because he had acted shrewdly; for the children of this age are more shrewd in dealing with their own generation than are the children of light. And I tell you, make friends for yourselves by means of dishonest wealth so that when it is gone, they may welcome you into the eternal homes.
‘Whoever is faithful in a very little is faithful also in much; and whoever is dishonest in a very little is dishonest also in much. If then you have not been faithful with the dishonest wealth, who will entrust to you the true riches? And if you have not been faithful with what belongs to another, who will give you what is your own? No slave can serve two masters; for a slave will either hate the one and love the other, or be devoted to the one and despise the other. You cannot serve God and wealth.’ ***
Over the years, in the organizations I worked for there was never an instance of embezzlement or fraud. It did happen close by a few times, and then it was that I learned from others the impact such dishonest behavior causes.
For years people have focused on this parable as a teaching about fraud and dishonesty. It is the most baffling of all the parables and raises thorny questions such as: Why does Jesus tell this story to his followers with such an unsavory character as a role model? Why does the rich man commend his manager for dishonesty?
I do not guarantee answers to those questions. But I promise to try. I hope that your takeaway includes thinking about the surprising ways God looks to us to engage in the work of advancing the Kingdom of God.
In the story, Jesus describes a boss and his manager who is about to be fired for “squandering” the boss’ property. The manager, knowing his time is short and his future prospects of employment are limited, goes to all the vendors who owe his boss. He convinces each of them to falsify their invoices to make it look like they owe less. The manager quickly wins the award for the most loved debt collector of the year.
When his boss finds out what the manager has done, he does not get angry. He commends the manager for acting shrewdly to save his own skin.
End of story. Now Jesus’ interpretation kicks in as he describes a world we know well. A world in which dishonesty, corruption, self-interest, rule the day. A world in which the absence of ethics, integrity and morality is so systemic, we barely notice much less protest.
From this point, the story sounds like it was ripped from the news headlines of the latest political or financial scandal. But then Jesus — the morally incorruptible, exemplar of ethics does something that nobody expects: He praises the corrupt manager!
How shocked are you? Even in this day when we have become numb to shameful behaviors and shock value rhetoric, I am not ready to have Jesus put a positive spin on deceitful actions. Is one of the takeaways of this parable that we are free and clear to cheat others when our own neck is on the line?
Of course, the answer is no! So why does Jesus praise the dishonest manager?
There are a couple of possibilities. It seems Jesus is trying to teach his disciples that being part of Body of Christ is not just about what is done using hands and feet. It is not just about the heart. Being part of the Body of Christ is also about the brain and using it to think critically.
If you have served on a nonprofit organization’s board or a church council you know there are usually two types of people at the table. Those who are passionate about issues worthy of addressing. Things like hunger, homelessness, poverty and the list goes on. There are also people who are focused on basic realities that have to be carefully managed and that usually has financial concerns. But there is a third type of people that are important and often missing at the table. They are the critical thinkers.
One of my favorite authors of biblical insight, the late Fred Craddock helps me understand the dishonest manager and why Jesus commends him. Craddock makes me look at Jesus as he uses the words “shrewdly” and “shrewdness” in describing the manager. These words trip me up. When Jesus uses them in praising the manager I think of him as cunning, a trickster. So, I label him a fraud and a cheat.
Yet, apart from my bias, shrewd people are critical thinkers who can see through situations and people with keen perception. Critical thinkers can navigate complex situations wisely and find effective solutions.
Regarding this story, Craddock advises not looking at the manager’s behavior. Rather he points to “Anti-cerebral bias in the church and the unwillingness…to conceive of thinking as a kingdom activity.”[i] In other words, critical thinking and people who possess that skill are important in the kingdom of God.
In praising the manager, Jesus is focused on his thinking ability — not highlighting his dishonesty. Jesus wants his disciples to see the manager’s ability for critical thinking as a tool in their work as disciples seeking to advance the Kingdom of God.
The focus on Critical Thinking to explain Jesus commending the dishonest manager is one possibility of where the Good News of God might leak from this baffling parable.
I want to propose another possibility. For every reason that we have to condemn the manager, there is an equally important reason to forgive him. This might be a stretch, but what if this parable is about forgiveness?
Jesus did say the manager is “dishonest in a very little,” but can we really be so sure that he is not also faithful in little, too? Are we not all a complicated mixture of faithfulness and frustration; of dishonesty and determination?
Perhaps the manager was a good father; a loving husband. Maybe he took care of the yard for his aging mother-in-law and shared fresh vegetables from his garden with local food pantry? We would consider him a good guy.
Yet, when we find ourselves facing someone’s immoral or unethical behavior, isn’t it a common tendency to jump to conclusions? We start critiquing that person’s actions and words — and even that person’s entire personality without knowing the whole story.
We begin to think of the person who committed the immoral or unethical behavior, not as a person who chose wrongly and made a mistake, but as a bad person. When we label the one who has offended or done wrong as a bad person then they become disposable — unworthy of our concern, undeserving of our forgiveness.
We have the tendency to label people in other ways, too: a person who commits a crime ceases to be a person and instead becomes a criminal. A person who enters the country without proper documents is demonized as an illegal immigrant. A person caught in the cycle of addiction disintegrates into the lexicon of drunk, junky, or stoner.
The language we use to refer to people whose behavior we find morally or ethically objectionable betrays us. They become something less than a person; someone unfit or unworthy of our care and concern.
Jesus’ praise of the manager is not an endorsement of unethical behavior. He reminds us that critical thinking is part of being a faithful disciple. And his praise of this manager is an affirmation of his personhood; as a beloved — albeit broken — part of the Body of Christ, and a builder of the Kingdom of God.
And at the end of the story, Jesus is calling us to second-guess ourselves; to re-evaluate our presuppositions and judgments. Because when we do that — when we lean on the side of mercy and forgiveness — the Kingdom of God becomes a little bigger, and the Body of Christ becomes a little stronger.
[i] Fred Craddock, “Luke” in Interpretation: A Bible Commentary for Preaching and Teaching (Louisville: John Knox Press, 1990), 191.
